遷移金属触媒を用いるフェノール類の脱芳香化反応を利用したスピロ環・縮環骨格合成法の開発

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  • Synthesis of Spirocyclic or Fused Cyclic Compounds Using Transition Metal-Catalyzed Dearomatization of Phenols
  • センイ キンゾク ショクバイ オ モチイル フェノールルイ ノ ダツホウコウカ ハンノウ オ リヨウ シタ スピロカン ・ シュクカン コッカク ゴウセイホウ ノ カイハツ

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This review describes the development of novel dearomatization reactions of phenols using transition metal catalysis. We found that an intramolecular ipso-Friedel-Crafts allylic alkylation of phenols proceeded smoothly in the presence of Pd catalyst, producing various spiro[4.5]cyclohexadienone derivatives. The present methods could be applied to a catalytic asymmetric reaction. An asymmetric intramolecular Friedel-Crafts allylic alkylation of phenols to produce chiral 10-vinyl 9,10-dihydrophenanthrenes was also investigated. The developed process was successfully applied to the enantioselective synthesis of bioactive natural products. We also developed a novel method for synthesizing spirocycles based on a Pd-catalyzed intramolecular ipso-Friedel-Crafts alkylation of phenols to η3-propargylpalladium(II) complexes. Mechanistic studies revealed that the present reaction proceeds through a rearomatization-assisited oxidative addition. An Au-catalyzed carbocyclization of phenols with a terminal alkyne via an intramolecular ipso-Friedel-Crafts alkenylation is also discussed.

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